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Ex-President Donald Trump has consistently shown his wish to see critics probed, exerting pressure on the Justice Department to charge former FBI Director James Comey and New York Attorney General Letitia James.

"We cannot postpone any longer, it's damaging our reputation and credibility," the president stated last month in a Truth Social message.

"I was impeached me, and charged me (five times!)" he said, referencing the multiple legal proceedings he faced after departing the White House in 2021 and James's lawsuit.

Each have subsequently been charged, in cases that numerous experts have stated appear to be driven by politics and challenging to win in legal proceedings.

But the most recent allegations against a Trump critic, former security advisor John Bolton, differ significantly, legal experts and former prosecutors say.

"In my opinion, contrasting Bolton's charges to Comey's is like equating two different things," stated Mark Lesko, a ex acting US attorney for the Eastern District of New York.

This Details of the Case

Bolton has been criminally indicted on national allegations pertaining to the alleged improper handling of sensitive materials. Since leaving the White House in 2019, he has emerged as a vocal presidential opponent, even to describe him "stunningly uninformed" and unsuitable for office in his memoir.

Experts contend that while there may be political motivations to target Bolton, the procedures used to obtain an charge and the proof gathered against him indicate a possibly more substantial legal argument than the DOJ brought against Comey.

"This misconduct that's being alleged is simultaneously more serious and seems to have taken place over a considerable duration," said Carissa Byrne Hessick, a academic at the University of North Carolina School of Law.

During his time as Trump's security advisor, and following his 2019 White House departure, authorities alleged that Bolton put the nation at risk by wrongfully keeping and sending classified information to relatives using insecure means, including AOL. Some of the materials were labeled top secret.

The charge states that at a certain time a hacker accessed to Bolton's system where documents were stored and transmitted an seeming warning to cause "the largest scandal since Hillary [Clinton]'s emails were leaked".

Bolton pleaded not guilty during a court appearance on Friday to eighteen distinct charges of mishandling classified information.

Retribution or a Substantial Case?

The schedule of his indictment - coming on the heels of charges against Comey - has revived concerns about external influence on the legal system.

Trump once implied Bolton should be in prison, and called him a "sleazebag". Bolton, for his role, wrote a book about his time in the Trump government that was sharply negative of the leader.

"Undoubtedly that the timing of this indictment, when combined with others, has raised doubts about the validity of these charges, and why these counts are being filed at this time," said Jamil Jaffer, creator and director of the National Security Institute.

Nevertheless, he added, "should the Justice Department is able to demonstrate the facts stated and demonstrate the material is properly designated, his behavior may very well have violated the statute".

Prosecuting such a high-ranking figure for mishandling sensitive materials is "rare" but not without precedent, said Carrie Cordero, a expert at the Center for a New American Security.

"Cases that involve sensitive materials pose difficulties to prosecute, but they can and are brought against equally junior and high-level personnel, from occasionally," she explained.

Parallels to Investigations into Trump and President

Trump similarly encountered allegations of wrongfully storing sensitive materials at his Mar-a-Lago property in Florida and obstructing their return, but that case was eventually thrown out by a court official and negated by his re-election as president.

A special counsel also found that former President Joe Biden improperly maintained classified documents from his period as vice president, but failed to criminally charge him.

Bolton's situation shares characteristics to Biden's sensitive materials matters, said Mr Lesko, who previously held a senior national security position at the DOJ.

Rigorous protocols regulate the management of sensitive materials. To win a conviction, the prosecution must demonstrate that Bolton knew the information he was transmitting was classified, and he had to knowingly transmit it to someone not entitled to obtain it.

"Because of the sensitive character of the information at question in this case, we lack a great deal of particulars about the reasons the prosecution believes elements like the diary entries and the other material he shared by email, and why there were restricted," explained Mr Jaffer.

A Increasingly Conventional Legal Action

The procedure by which the DOJ brought this case will be under scrutiny, after Trump publicly posted his desire to see his critics prosecuted and some of those indictments materialized.

But Mr Lesko indicated in Bolton's situation, prosecutors appear to have followed protocol.

"This Bolton prosecution and eventually the indictment appeared to have observed the regular process including the regulations and standards within the Department of Justice," he stated.

Unlike Comey's brief, concise charge, Bolton's was a more "traditional" filing that "explicitly outlines the details involving the circumstances and situation here," Mr Lesko commented.

"It appears fairly consistent with a series of precedents... where government officials mishandled and transmitted classified material."